Just around the start of the 20th century O. W. Gurley, a wealthy African American land-owner from Arkansas, traversed the United States to participate in the Oklahoma Land run of 1889. The young entrepreneur had just resigned from a presidential appointment under president Grover Cleveland in order to strike out on his own.

In 1906, Gurley moved to Tulsa where he purchased 40 acres of land which was "only to be sold to colored". Black ownership was unheard of at that time.

An educator and entrepreneur who made his wealth as a landowner, Gurley purchased 40 acres in Tulsa to be sold to “coloreds only.” Senate Bill Number 1, the state’s first piece of legislation, prevented coloreds from residing, traveling and marrying outside their race. Gurley’s property lines were Pine Street to the north, the Frisco rail tracks to the south, Lansing Avenue to the east and Cincinnati Avenue to the west.
Among Gurley's first businesses was a rooming house which was located on a dusty trail near the railroad tracks. This road was given the name Greenwood Avenue, named for the city in Mississippi. The area became very popular among African American migrants fleeing the oppression in Mississippi. They would find refuge in Gurley's building, as the racial persecution from the south was non-existent on Greenwood Avenue.

In addition to his rooming house, Gurley built three two-story buildings and five residences and bought an 80-acre (320,000 m2) farm in Rogers County. Gurley also founded what is today Vernon AME Church.

In the 1830s, many African Americans journeyed to what would later be called Oklahoma, experiencing undesirable hardships along the Trail of Tears with the Five Civilized Tribes. Under President Andrew Jackson’s administration, the Indian Removal Act relocated the tribes and their slaves to the established Twin Territories. Of the thirty-two black townships that were established in America after the civil war, twenty-eight of them were in Oklahoma before it became a state. Gurley, one of Tulsa’s earliest pioneers, named the Greenwood district.
The still-unpaved streets would also serve as Tulsa’s racial dividing lines. After Gurley’s purchase of the land, Tulsa began to grow. Black ownership was unheard of at that time, but under the state’s Jim Crow laws, Greenwood was born out of necessity.

The racial climate prevented Blacks from shopping anywhere but Greenwood. Among Gurley’s first businesses was a boarding house located on a dirt road crossing the Frisco tracks, which would later be named Greenwood Avenue.
By 1913, more businesses followed, including law and doctors’ offices of Buck Colbert Franklin and A.C. Jackson respectfully, Dunbar and Booker T. Washington schools, Vernon AME, and Mount Zion Baptist churches, Ricketts’ Restaurant, The Williams’ Dreamland Theater, Mann’s Grocery Stores, Stradford Hotel, and a host of haberdasheries, drug stores, cafes, barbershops and beauty salons.

This implementation of "colored" segregation set the Greenwood boundaries of separateness that exist here in 2014: Pine Street to the North, Archer Street and the Frisco tracks to the South, Cincinnati Street on the West, and Lansing Street on the East. The segregation is pronounced in subtle landmarks. South of Archer, Greenwood Avenue does not exist in white neighborhoods.
Another African American entrepreneur, J.B. Stradford, arrived in Tulsa in 1899.

He believed that black people had a better chance of economic progress if they pooled their resources, worked together and supported each other's businesses. He bought large tracts of real estate in the northeastern part of Tulsa, which he had subdivided and sold exclusively to other African Americans. A number of other blacks soon followed suit. Stradford later built the Stradford Hotel on Greenwood, where blacks could enjoy the amenities of the downtown hotels who served only whites. It was the largest black-owned hotel in the United States.

Gurley's prominence, influence and wealth were short lived. In a matter of moments, he lost everything. During the race war, The Gurley Hotel at 112 N. Greenwood, the street’s first commercial enterprise, valued at $55,000, was lost, and with it Brunswick Billiard Parlor and Dock Eastmand & Hughes Cafe. Gurley also owned a two-story building at 119 N. Greenwood. It housed Carter’s Barbershop, Hardy Rooms, a pool hall, and cigar store. All were reduced to ruins. By his account and court records, he lost nearly $200,000 in the 1921 race war.

Because of his leadership role in creating this self-sustaining exclusive black "enclave", it had been falsely rumored that Gurley was lynched by a white mob and buried in an unmarked grave. However, according to the memoirs of Greenwood pioneer, B.C. Franklin, Gurley exiled himself to California. The founder of the most successful African American community of his time vanished from the history books and drifted into obscurity. He was honored in a 2008 documentary film called, Before They Die! The Road to Reparations for the 1921 Tulsa Race Riot Survivors.